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Sodium Bicarbonate → 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-N-methyl-1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-4-carboxamide

HRID 39787
ノート
印刷プレビュー

反応式

HRID 39787 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3([C:19]([NH:21][CH3:22])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[O:23]=[C:24]1[CH:33]=[N:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]1[CH2:34][CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3([C:19]([NH:21][CH3:22])=[O:20])[CH2:14][CH2:15][N:16]([CH2:35][CH2:34][N:25]4[C:26]5[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=5)[N:32]=[CH:33][C:24]4=[O:23])[CH2:17][CH2:18]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59397888(2-oxoquinoxalin-1(2H)-yl)acetaldehydeHCID 59398153HCID 59398153、化合物

生成物 1

HCID 593978244-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-N-methyl-1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-4-carboxamide収率 72.7%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To 3 mL of dichloromethane solution containing 0.11 g of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-N-methylpiperidine-4-carboxamide, 65 mg of (2-oxoquinoxalin-1(2H)-yl)acetaldehyde and 20 μL of acetic acid were added and stirred at room temperature for 3 hours. To the reaction mixture, 0.11 g of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to give 0.12 g of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-N-methyl-1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-4-carboxamide as a yellow oil.

後処理

  1. additionwere added
  2. stirringstirred at the same temperature for 30 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed sequentially with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

出典と根拠

ORDレコード
ord-37d33b38d0fc497bb8da6889ca5e6205
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524738B2

反応ノート

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